Benzoyl isothiocyanate → HCID 86640986, compound

HRID 1972170Notes

Reaction equation

HRID 1972170 reaction equation
[Br:1][C:2]1[C:3]([O:9][C:10]2[C:11]([CH3:16])=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:17]([N:25]=[C:26]=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[C:17]([NH:25][C:26]([NH:8][C:5]1[CH:4]=[C:3]([O:9][C:10]2[C:11]([CH3:16])=[N:12][CH:13]=[CH:14][CH:15]=2)[C:2]([Br:1])=[CH:7][N:6]=1)=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67486270HCID 67486270, compound

Product 1

HCID 86640986HCID 86640986, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-4-(2-methylpyridin-3-yloxy)pyridin-2-amine (2.0 g, 7.14 mmol) and benzoyl isothiocyanate (1.0 ml, 7.5 mmol) were diluted in tetrahydrofuran (100 mL) and stirred at ambient temperature overnight. The solution was concentrated and charged with a mixture of ethyl acetate (10 mL) and hexanes (200 mL). The mixture was stirred for 10 minutes and filtered to give the title compound (2.8 g, 89% yield) as yellow solid.

Workup

  1. concentrationThe solution was concentrated
  2. additioncharged with a mixture of ethyl acetate (10 mL) and hexanes (200 mL)
  3. stirringThe mixture was stirred for 10 minutes
  4. filtrationfiltered

Sources & evidence

ORD record
ord-7f6b2e00a264442cb6666f1c74d9e623
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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